


The Games Begin

by braezenkitty



Series: Unexpected [3]
Category: Supernatural
Genre: Friends to Lovers, Gaming, I'm Sorry, Kissing, Making Out, Mario Kart, Multi, No Sex, Nudity, Strip Games
Language: English
Status: Completed
Published: 2019-02-01
Updated: 2019-02-01
Packaged: 2019-10-20 07:42:20
Rating: Mature
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,923
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/17618297
Author URL: https://archiveofourown.org/users/braezenkitty/pseuds/braezenkitty
Summary: Dean, Cas, and Jimmy have their dinner date, and play some games.





	The Games Begin

**Author's Note:**

> I’ve only ever played Mario Kart as a small child or while drunk, so if I got anything about the game mechanics wrong (for instance how long it takes for a car to be put back onto Rainbow Road after falling off and whether that's enough time for a person to remove an article of clothing) I shouldn’t be held accountable lol. Just roll with it.
> 
> Written for the SPN Kink Bingo  
> Square filled: Friends to Lovers

Dean stepped out of the shower and grabbed his towel. As he dried himself off, he switched his phone screen on so he could check the time. Cas would be home any minute. Jimmy would already be home, since his job allowed him to work remotely, so Dean could go over now. But he wanted to wait a bit, let Cas get home and get settled, have some time to change or whatever. Kiss Jimmy hello without Dean there to make it weird.

Thinking about Cas and Jimmy kissing made his cock twitch and he scowled at it. He’d already jerked off three times since last night when he’d walked in on Jimmy naked and blindfolded and obviously waiting for Cas: once almost as soon as he got home, once this morning, and once just now in the shower so he wouldn’t be walking around with a raging boner in Cas and Jimmy’s presence. He was obviously sexually attracted to them and was totally into the idea of having sex with the both of them, but they were also his friends, and he didn’t want to objectify them. Having them think he just wanted them for the kinky twin sex factor was not at all what he wanted, because it wasn’t true. He wanted more than just sex, had for a long time. He’d just never thought it was possible until last night.

Hanging his towel on a hook, he grabbed his phone off the bathroom counter and stepped out into his bedroom. He stopped in front of his dresser and checked his phone one more time before setting it down. No messages from Cas or Jimmy yet. Part of him wondered if he had dreamed up what had happened last night. Maybe he should text them and double check that he should still come over.

He was about to type out a message when a new text popped up in his group chat with Cas and Jimmy.

 **Cas 5:42pm** Hello Dean. I’m home. Come over any time.

Dean grinned and typed a response.

 **Dean 5:43pm** Just getting dressed and I’ll be on my way

 **Jimmy 5:43pm** Does that mean you’re naked right now? You can just come over like that if you want

 **Cas 5:44pm** What my horndog brother meant to say is take your time, there’s no rush and no expectations

Dean smiled to himself and shook his head at Jimmy’s blatant flirtation.

 **Dean 5:44pm** Got it, be over soon

Apparently he hadn’t imagined the situation, and it also appeared that Jimmy at least was as into the idea of having sex as Dean was. Cas was a bit of an enigma, as usual, but he’d feel things out as the night went on. No need to rush, as Cas had said. They’d been friends for months and Dean didn’t want to ruin that friendship by moving things too quickly.

He pulled open his underwear drawer and his hand hovered over a pair of plain boxer briefs, but despite not wanting to rush things he did want to feel sexy. And what were the odds of them actually having sex tonight? He might as well wear the panties he saved for the times when he wanted to feel especially sexy. He chose a pair of pink satin ones with a little bit of lace around the edges and pulled them on, then dug out a pair of comfy, well worn jeans and a soft black t-shirt. He pulled a blue button down on over the t-shirt, put on socks and boots, then put a little gel in his hair and some deodorant on and he was ready to go.

Before he knew it, he stood outside of Jimmy and Cas’ door, his stomach full of butterflies. He knocked.

A moment later, Cas opened the door, still in his dress pants, shirt and tie from work, though the tie was loosened and his feet were clad only in socks. He smiled. “Hello, Dean.”

“Hey, Cas,” Dean said, grinning back.

“You gonna let him in or make him stand on the porch all night?” Jimmy called as he walked out of the kitchen, three beer bottles in hand. “Hey, Dean,” he said as he came up behind Cas. “You know you don’t have to knock anymore.”

“Yeah, well I wouldn’t want to walk in on anything I wasn’t meant to see,” Dean said, winking at Jimmy.

Jimmy actually blushed, though he rolled his eyes.

“I’m very sorry about that, Dean,” Cas said seriously, then stepped back and held the door open. “Please come in.”

“You don’t have to keep apologizing,” Dean said, stepping inside and kicking his boots off in the designated area by the door. The smell of cooking food hit his nostrils and he inhaled deeply. Cas closed the door behind him and Jimmy handed him a beer. “Thanks,” he said, taking the beer. “Something smells good.”

“That would be Jimmy’s roasted chicken and root veggies.” Cas gave Jimmy a quick smile. “He wanted to impress you.”

“Well, color me impressed,” Dean said as they moved into the living room. Jimmy flopped on the couch in his usual corner.

“We’re glad you decided to come over,” Cas said, placing a hand on Dean’s shoulder and giving it a quick squeeze.

“Yeah, we were a bit worried you’d run for the hills after finding out… about us.”

“You guys are like my best friends,” Dean said as he sat in the middle of the couch, leaving the other corner for Cas. “Besides Charlie and Sam. It’s definitely unexpected, but not weird enough to make me want to run away.”

They fell into a somewhat awkward silence, none of them quite sure where to go from there.

“Have you guys told a lot of people?” Dean asked.

“No,” Cas and Jimmy answered in unison. It always made Dean chuckle when they did that.

“Our parents know. They found us together one night,” Jimmy said, then took a sip of his beer.

“They weren’t happy, to say the least,” Cas said, picking at the label on his bottle.

“Luckily we were old enough to move out, so we did. Pretty sure they told the whole family because we never hear from any of them anymore. They all stopped responding to our efforts to reach out.”

“Jeez,” Dean said, “that sucks.”

“Yeah,” Cas said sadly. “We told an ex of mine, Meg. She was surprisingly okay with it.”

“A little too okay,” Jimmy said with a shudder. “I wasn’t into her at all, and she wouldn’t stop trying to force us into a threesome.”

“Had to break up with her, and she got so pissed she told all our friends about us. So of course they all stopped talking to us.”

“Shit,” Dean said.

“Another time, we were both into this guy named Balthazar,” Jimmy said. “He seemed really open minded, but turned out not to be at all. That didn’t end well.”

“No,” Cas said, shaking his head, “but he at least kept quiet about it.”

“So you guys thought you were going to lose me too?”

“Can you blame us?” Jimmy asked with a sad smile.

“Everyone either fetishises us, or walks away,” Cas said, his smile mirroring the sadness in Jimmy’s.

“Shit, I’m sorry,” Dean said, looking between the two of them. “For the record, I’m not going to do either of those things.”

“Thank you, Dean,” Cas said with a little more warmth in his smile.

“We should also clarify,” Jimmy said, looking a bit rueful, “that despite my earlier text about your state of dress, we don’t expect anything sexual from you. Our friendship can stay just as it is—a friendship and nothing more—if that’s what you want.”

“Okay,” Dean said, then took a sip of his beer to give himself a moment. “But what if that’s what I want? What if I want friendship and sex? Like, not objectifying sex, and I wouldn’t fetishise you, but what if I wanted to like, date you? Both of you?”

Cas and Jimmy’s smiles grew. “We’re definitely open to that,” Cas said and Jimmy nodded in agreement.

“Fully on board with that,” Jimmy said, letting loose a relieved laugh.

“Awesome,” Dean said, smiling shyly and biting at his lip. “So what now?”

A timer sounded from the kitchen before anyone could answer. “Now, we eat,” Jimmy said with a grin as he jumped up from the couch and rushed off to the kitchen.

Cas stood and held a hand out to Dean, keeping eye contact while Dean stood. “I’m really glad you’re here, Dean,” he said, then leaned forward to kiss Dean on the cheek.

Dean could feel a blush spread over his cheeks as he responded. “Me too.”

Cas squeezed his hand and let go, grabbing his beer off the end table and walking towards the kitchen. Dean grabbed his beer off the coffee table and followed. When they reached the kitchen, Cas walked up behind Jimmy and kissed the back of his neck, placing his hands on Jimmy’s hips and looking over his shoulder.

“Looks delicious,” Cas said as Jimmy carved the chicken.

“Thanks,” Jimmy said with a smile, and Dean found his fingers itching to reach out and get in on their casual affection. It had been so long since he’d been with somebody, let alone two somebodies who he’d had a crush on for months.

Jimmy looked over and smiled at him, and as if he’d been reading Dean’s mind he said, “Get over here, Dean.”

Dean huffed a laugh and stepped closer. Cas grabbed him around the waist, positioning him between him and Jimmy. Dean wrapped his arms around Jimmy’s waist and rested his chin on Jimmy’s shoulder, watching him work. Cas rested his chin on Dean’s opposite shoulder, watching from the other side. It was nice, domestic even, and it was everything Dean had been craving for months.

“Is this okay, Dean?” Cas asked, his voice pitched low in Dean’s ear. Dean’s cock perked up and he had to remind himself that he wanted to take things slow.

“Yeah,” he said, ignoring his dick, “this is good.”

“Good,” Jimmy said, twisting to place a kiss on Dean’s cheek. “But this chicken is done, so get off me and let’s eat.”

Dean laughed and let his hands drop, stepping back and following Jimmy to the dining room where he set the platter of carved chicken and root vegetables on the table. The table was already set with three place settings. Dean sat at one and Cas and Jimmy sat on either side of him. He could really get used to being in the middle of them.

Dinner was full of smiles and laughter, much the same as all their previous dinners as friends, only with lots more flirting and banter and blushing all around. When they finished, they all worked together to clear the table, put away the leftovers, and wash the dishes, leaving the kitchen clean and tidy. Jimmy suggested they play a video game when they finished.

“Only if you don’t cheat,” Dean said.

“What? Me, cheat? How dare you insinuate such a thing.”

“You do regularly cheat using distraction and other means of giving yourself advantage,” Cas said, raising an eyebrow at Jimmy as he walked to the living room.

“I’m offended.” Jimmy flopped onto the couch, arms crossed and bottom lip stuck out in a pout.

Cas rolled his eyes and walked over to the TV to pick up the controllers and turn the system on. Dean flopped down next to Jimmy, letting his head fall to the side to give Jimmy a teasing look. “Maybe you shouldn’t cheat, then.”

“How do I cheat? Give me one example.”

Dean huffed a laugh. “Like Cas said, you use distraction. Sitting over there with your gorgeous blue eyes and messy hair, looking all sexy.”

“He has a point,” Cas said, handing them each a controller.

“You think I’m sexy?” Jimmy asked, waggling his eyebrows at Dean. “Enough to be distracting?”

Dean blushed and turned his attention to the TV. “You’re alright,” he said with a shrug.

“Well,” Jimmy said, leaning over so his shoulder pressed against Dean’s, “it’s not my fault you two can’t stay focused on the game. And if I’m cheating by looking sexy, then so are you two. I’m just better at disregarding it and staying focused.”

“That sounds like a challenge,” Dean said with a grin at Cas.

Cas grinned back at him. “It does.”

“That was not a challenge,” Jimmy said sternly, keeping his attention on the TV while flipping through the game choices.

Dean laughed. “Put on Battlefront.”

“You’re such a Star Wars nerd,” Jimmy said teasingly.

“Hey, you’re the one who owns the game,” Dean quipped back.

“Yeah, because I wanted to get you over here to play games more often,” Jimmy retorted.

“Aww, you like me.”

“Do not.”

“Okay, children,” Cas said, knocking his shoulder into Dean’s, thus knocking Dean into Jimmy. “How about we play Mario Kart, that way we can all play at the same time.”

“That’ll work,” Dean said.

“Shall we make a wager on who’s going down first?” Cas asked

Jimmy and Dean snickered.

“Not that kind of going down,” Cas said sternly.

“You’re no fun,” Jimmy pouted.

“Oh, I bet he’s plenty of fun,” Dean said, winking at Cas.

Cas huffed a laugh, blushing as he fiddled with the game controller.

“Cute, too,” Dean said, bumping Cas’ shoulder and smiling at him before turning back to the game.

“You guys are both adorable,” Jimmy said, “but it’s game time so knock it off.”

“Yes, sir,” Dean said with a cheeky grin.

Jimmy laughed. “I like that.” He started the game and selected a track.

“Seriously?” Dean scoffed. “You’re gonna start us on Rainbow Road?”

“Heck yeah, you know I love a challenge,” Jimmy said with a laugh. “And we can make it more interesting… if you want.”

“More interesting… how?” Dean asked.

“We play with house rules.”

“Jimmy,” Cas warned. “I thought we were going to take things slow?”

Dean looked from Cas back to Jimmy. “Wait, we’ve played this dozens of times and there have never been house rules before.”

Jimmy grinned. “That’s because house rules have always been just for Cas and I, for reasons that will become obvious.”

“Okay.” Dean raised an eyebrow.

“House rules,” Cas said, “are you remove one piece of clothing every time you fall off the track.”

Dean blinked. He thought about how many times he’d fallen off Rainbow Road. He mentally counted the number of clothing articles he had on. There was a damn good chance he’d end up completely naked, or close to it, by the end of the first round, if he wasn’t careful.

“Remember, Dean, there are no expectations,” Cas said. “We can play without house rules.”

“Yeah, totally up to you,” Jimmy said, bumping his shoulder and giving him a small smile.

Dean nodded, then thought of something. “You said house _rules_. Plural.”

“I did,” Jimmy said, flicking his gaze to Dean then back to the TV.

Dean turned to Cas, waiting for one of them to answer.

Cas cleared his throat and Dean noticed a blush spread over his cheeks. “Second house rule is the loser has to blow the winner.”

“Oh,” Dean said, feeling his own cheeks heat.

“But we don’t have to play with that rule,” Jimmy said quickly. “That’s hard mode… literally.” He snickered. “We can play on easy mode.”

Dean laughed, fidgeting with his controller. Part of him really wanted to play on hard mode, but he also didn’t want to rush into things and make Jimmy and Cas think he only wanted them for sex. Even though he really, really did, it wasn’t all he wanted. He wanted more dinners, more game nights, real intimacy… not just sex.

“How about we play easy mode this round,” Cas suggested, smiling at Dean, “then we reevaluate.”

“Yeah, okay,” Dean said, smiling back. Sex wasn’t ruled out, but it wasn’t the focus up front either. That was good.

“Alright,” Jimmy said. “Let’s do this. I’m gonna kick both your asses.”

“You wish,” Dean said with a laugh.

Cas snorted. “Bring it on.”

They proceeded to choose their characters—Jimmy ended up with Yoshi, Cas chose Toad, and Dean went with Princess Peach. The race started, and they all took off, zooming down the Rainbow Road. Cas was the first to fall off, and he pulled off his socks while waiting for his car to make it back onto the road. Dean fell off next, and he also pulled his socks off. Jimmy was left in the lead, cackling obnoxiously as Dean and Cas both tried hopelessly to catch up. But then Jimmy fell off, much to Dean and Cas’ amusement. He wasn’t wearing any socks, so he pulled off his zip up hoodie. By the end of the race, Cas and Dean had each fallen off twice more, Jimmy had fallen off once more and all three were shirtless.

“Told you I was gonna kick your asses,” Jimmy said with a smirk while they waited on the loading screen.

“Dude, you finished in 5th place,” Dean said.

“Yeah, but you finished in 7th and Cas was in 8th.”

“Clearly we all win,” Cas said, raising an eyebrow at Dean and Jimmy, “because we’re all half naked.”

“Excellent point,” Jimmy said. “Ready for the next race?”

Dean thought about what would happen if they kept playing with the house rules—if he fell again, he’d end up having to take his jeans off, and then his panties would be revealed. But he was warmed up now, and he figured if he kept it slow and steady, he’d have a good chance of staying on the track, if not winning. “Alright,” he said, “you’re on.”

“Cas?”

“I’m not letting you win by default. Of course I’m in.”

The race started and they all took off. Dean ended up in last place pretty quickly, not wanting to fall off the track. After a couple laps, Jimmy fell off and quickly shucked his sweatpants off. Dean was so distracted by the appearance of Jimmy’s thick thighs and cute ass in tight, black boxer briefs that he drove right off the road.

“Shit,” he mumbled.

“You know the rules, Winchester,” Jimmy said with a snicker.

Dean stood and quickly unbuttoned his pants, pulling them off in one go.

“Holy shit, Dean,” Jimmy breathed. “Are you wearing panties?”

Cas groaned next to him and Dean smiled shyly. “Yeah.”

It was Jimmy’s turn to groan, and he promptly fell off the edge of the track.

Dean laughed. “Well, Novak, you know the rules.”

Jimmy set his controller down on the table, then stood and pulled his boxer briefs off, stepping out of them before sitting back down.

“Fuck,” Dean breathed. Jimmy was full on naked, his gorgeous cock half hard, and Dean couldn’t tear his eyes away.

Jimmy cleared his throat. “My eyes are up here.”

“Shit,” Dean said, snapping his gaze back to the TV where he realized he’d fallen off the track. “Oh, goddammit.”

“Leave them on,” Cas said gruffly. He kept his eyes on the TV and his car on the road. He’d somehow managed not to fall off once this round, and was still in his dress pants, although Dean noticed an obvious bulge in the front when he glanced over at him.

“Okay,” Dean said.

“I think you’ve won, Cas,” Jimmy said with a laugh. “You can probably stop now.”

“You’re absolutely right,” Cas said, setting his controller down on the coffee table, letting Toad drive off the road. He turned back to Dean. “May I kiss you now?”

Dean huffed a laugh, his cock twitching in his panties. So much for taking things slow. “Hell yeah,” he breathed.

Cas placed a hand on Dean’s cheek, turning him slightly, then leaned in and pressed his lips to Dean’s. An involuntary moan rumbled up from Dean’s chest as he fisted a hand in Cas’ hair and held him close. He opened to Cas, their tongues sliding together languorously, and lost himself in the kiss until he felt another hand slide across his stomach. He broke off from the kiss and turned to find Jimmy. He licked his lips and leaned forward, capturing Jimmy’s mouth.

Jimmy kissed more insistently than Cas, less hesitantly, and the kiss quickly became heated. Dean nipped at Jimmy’s bottom lip, drawing a gasp from him that went straight to Dean’s cock. He found himself wishing Cas’ hand on his thigh would move up a little farther, but then he was distracted by Cas’ lips on that soft, sensitive spot behind his ear, kissing and licking down his neck.

He broke off from Jimmy’s kiss to breathe, found Jimmy staring at him with darkened eyes. He smirked at Dean, then moved to kiss Dean’s shoulder and across his collarbone.

“Jesus,” he breathed, “you two are gonna be the death of me.”

Cas and Jimmy both chuckled, their breath hot on Dean’s neck and chest. “Hopefully only le petite mort,” Cas mumbled against his skin, moving up to kiss him again.

Dean’s cock throbbed and he moaned into Cas’ mouth. He was fully hard now, his cock trying to pop out of his panties, and Cas speaking French wasn’t helping the situation. Cas’ hand on his thigh wasn’t helping either, especially when it kept creeping farther up his leg. He needed someone to touch him, or he needed this to stop.

“Fuck,” he gasped as Jimmy’s mouth moved to his nipple. “Okay, okay, guys,” he said, squeezing Jimmy’s bicep and the back of Cas’ neck, “hold up.”

Cas and Jimmy both instantly stopped and sat back, removing their hands from his body. He ached at the loss, while simultaneously rejoicing at the fact that they stopped so quickly at his word.

“I’m so sorry, Dean,” Cas said quickly. “I didn’t mean to push you into anything.”

“Yeah, that was not our intent—not _my_ intent. I’m sorry, Dean,” Jimmy said, looking at Dean seriously.

“It’s fine,” Dean said with a smile, pulling them closer, though they kept their hands to themselves. “I just wanted a breather, because if we keep going… well, let’s just say we’re fast approaching the point of no return, if you know what I mean.”

“I think we do,” Cas said with a relieved laugh.

“Definitely,” Jimmy agreed, glancing down at his cock, which still stood at attention, dribbling precum.

“Shit,” Dean mumbled as he openly stared for a moment before dragging his eyes away. “Shit. Okay. So here’s the deal. I want to have sex with you guys.”

“Okay,” said Cas.

“On board, fully,” said Jimmy.

Dean laughed. “But I don’t want us to rush into anything without making sure we’re all on the same page.”

“I think we’re on the same page,” Jimmy said. Cas nodded.

“Okay, good,” Dean said, taking in the gorgeous twin smiles and sets of deep blue eyes watching him. “Continue, then,” he said with a cheeky grin.

Cas and Jimmy both rolled their eyes. “You’re lucky we like you,” Jimmy joked, moving in to kiss Dean. Cas put his hand back on Dean’s thigh, fingers edging the lace on Dean’s panties.

“And we really,” Cas said, kissing Dean’s neck, “like you.”

Dean groaned as Jimmy’s fingers brushed over his nipple. “Really like you too,” he said breathlessly, “both of you.”


End file.
